ADAMANTANE DERIVATIVES - VARIETY OF BIOLOGICAL ACTIVITIES. A REVIEW OF MEDICATIONS APPROVED IN POLAND AND POTENTIAL DRUGS
DOI:
https://doi.org/10.56782/pps.88Keywords:
adamantane derivatives, antiviral activity, antiparkinsonian activity, antidiabetic activity, Alzheimer’s diseaseAbstract
Adamantyl-based compounds of varied structures are used for the treatment of neurological disorders, such as Parkinson’s disease and Alzheimer’s disease, in the therapy of type 2 diabetes mellitus and as antiviral agents. Adamantyl group determine the therapeutic properties of plain adamantylamines. In the other compounds the steric bulk of the adamantyl group increases the drug stability due to the limitation of intramolecular reactivity. The adamantyl group is valuable in drug design and development. Such derivatives are under studies as potential anti-HIV agents or for treating malaria.
Downloads
References
R.C. Fort, P.R. Schleyer, Chem. Rev., 1964, 64, 277-300. DOI: https://doi.org/10.1021/cr60229a004
Pharmindex ’11 Kompendium leków, UBM Medica Poland, 2011.
M.G. Alves Galvão, M.A. Rocha Crispino Santos, A.J.L. Alves da Cunha, Amantadine and rimantadine for influenza A in children and the elderly. Cochrane Database of Systematic Reviews, 2008, 1. Art. No.: CD002745. DOI: 10.1002/14651858.CD002745.pub2. DOI: https://doi.org/10.1002/14651858.CD002745.pub2
S.D. Cady, W. Luo, F. Hu, M. Hong, Biochemistry, 2009, 48, 7356-7364. DOI: https://doi.org/10.1021/bi9008837
S.D. Cady, K. Schmidt-Rohr, J. Wang, C.S. Soto, W.F. DeGrado, M. Hong, Nature,. 2010, 463 (7281), 689-693. DOI: https://doi.org/10.1038/nature08722
M.R. Rosenberg, M.G. Casarotto, PNAS, 2010, 107 (31), 13866-13871. DOI: https://doi.org/10.1073/pnas.1002051107
T. Jefferson, V. Demicheli, C. Di Pietrantonj, D. Rivetti, Amantadine and rimantadine for influenza A in adults, Cochrane Database of Systematic Reviews, 2006, 2. Art. No.: CD001169. DOI: 10.1002/14651858.CD001169.pub3. DOI: https://doi.org/10.1002/14651858.CD001169.pub3
P.S. Manchand, R.L. Cerruti, J.A. Martin, C.H. Hill, J.H. Merrett, J. Med. Chem. 1990, 33, 1992-1995. DOI: https://doi.org/10.1021/jm00169a029
J.W. Tilley, M.J. Kramer, Progr. Med. Chem., 1981, 18, 1-44. DOI: https://doi.org/10.1016/S0079-6468(08)70315-1
I. Stylianakis, A. Kolocouris, N. Kolocouris, G. Fytas, G.B. Foscolos, E. Padalko, J. Neyts, E. De Clercq, Bioorg. Med. Chem. Lett., 2003, 13, 1699-1703. DOI: https://doi.org/10.1016/S0960-894X(03)00231-2
K. Lundahl, J. Schut, J.L. Schlatmann, G.G. Paerels, A. Peters, J. Med. Chem. 1972, 15, 129-132. DOI: https://doi.org/10.1021/jm00272a003
G. Stamatiou, G.B. Foscolos, G. Fytas, A. Kolocouris, N. Kolocouris, C. Pannecouque, M. Witvrouw, E. Padalko, J. Neytsb, E. De Clercqb, Bioorgan. Med. Chem., 2003, 11, 5485-5492. DOI: https://doi.org/10.1016/j.bmc.2003.09.024
Z.M. Younossi, R.P. Perrillo, Semin. Liver Dis., 1999, 19 Suppl 1, 95-102. DOI: https://doi.org/10.1055/s-2007-1007092
S.D. Griffin, L.P. Beales, D.S. Clarke, O. Worsfold, S.D. Evans, J. Jaeger, M.P. Harris, D.J. Rowlands, FEBS Lett., 2003, 535, 34-38. DOI: https://doi.org/10.1016/S0014-5793(02)03851-6
E. Steinmann, T. Whitfield, S. Kallis, R.A. Dwek, N. Zitzmann, T. Pietschmmann, R. Bartenschlager, Hepatology, 2007, 46, 330-338. DOI: https://doi.org/10.1002/hep.21686
K.S. Rosenthal, M.S. Sokol, R.L. Ingram, R. Subramanian, R.C Fort, Antimicrob Agents Chemother., 1982, 22, 1031-1036. DOI: https://doi.org/10.1128/AAC.22.6.1031
Mack R. Holdiness, Contact Dermatitis, 2001, 44, 265-269. DOI: https://doi.org/10.1034/j.1600-0536.2001.440501.x
A. Kreutzberger, H.H. Schroeders, Tetrahedron Lett. 1969, 58, 5101-5104. DOI: https://doi.org/10.1016/S0040-4039(01)88894-8
K. Van Derpoorten, J. Balzarini, E. De Clercq, J.H. Poupaert, Biomed. Pharmacother. 1997, 51, 464-468. DOI: https://doi.org/10.1016/S0753-3322(97)82327-X
J. Balzarini, B. Orzeszko, J. K. Mauri, A. Orzeszko, Eur. J. Med. Chem. 2007, 42, 993-1003. DOI: https://doi.org/10.1016/j.ejmech.2007.01.003
R.S. Schwab, D.C. Poskanzer, A.C. England, Jr., R.R. Young, JAMA, 1972, 222, 792-795. DOI: https://doi.org/10.1001/jama.222.7.792
W. Danysz, C.G. Parsons, J. Kornhuber, W.J. Schmidt, G. Quack, Neurosci. Biobehav. Rev., 1997, 21, 455-468. DOI: https://doi.org/10.1016/S0149-7634(96)00037-1
K. Mizoguchi, H. Yokoo, M. Yoshida, T. Tanaka, M. Tanaka, Brain. Res. 1994, 662, 255-258. DOI: https://doi.org/10.1016/0006-8993(94)90821-4
P. Camps, M.D. Duque, S. Vázquez, L. Naesens, E. De Clercq, F.X. Surenda, M. López-Queol, A. Camins, M. Pallàs, S.R. Prathalingam, J.M. Kelly, V. Romero, D. Ivorra, D. Cortés, Bioorg. Med. Chem., 2008, 16, 9925-9936. DOI: https://doi.org/10.1016/j.bmc.2008.10.028
N. Crosby, K.H.O. Deane, C.E. Clarke, Amantadine in Parkinson’s disease. Cochrane Database of Systematic Reviews, 2003, Issue 1. Art. No.: CD003468. DOI: 10.1002/14651858.CD003468. DOI: https://doi.org/10.1002/14651858.CD003468
R. McShane, A. Areosa Sastre, N. Minakaran, Memantine for dementia. Cochrane Database of Systematic Reviews, 2006, Issue 2. Art. No.: CD003154. DOI: 10.1002/14651858.CD003154.pub5. DOI: https://doi.org/10.1002/14651858.CD003154.pub5
L.I. Kas’yan, D.V. Karpenko, A.O. Kas’yan, A.K. Isaev, S.A. Prid’ma, Russ. J. Org. Chem. 2007, 43, 1642-1650. DOI: https://doi.org/10.1134/S1070428007110103
G. Zoidis, I. Papanastasiou, I. Dotsikas, A. Sandoval, R. G. Dos Santos, Z. Papdopoolou-Daifoti, A. Vamvakides, N. Kolocouris, R. Felix, Bioorg. Med. Chem., 2005, 13, 2791-2798. DOI: https://doi.org/10.1016/j.bmc.2005.02.030
T.W. von Geldern, J.M. Trevillyan, Drug Dev. Res., 2006, 67, 627-642. DOI: https://doi.org/10.1002/ddr.20138
Charakterystyka produktu leczniczego: http://www.ema.europa.eu/docs/pl_PL/document_library/EPAR_-_Summary_for_the_public/human/000771/WC500020328.pdf
J.U. Peters, Curr. Top. Med. Chem., 2007, 7 (6), 579-595. DOI: https://doi.org/10.2174/156802607780091000
S.H. Havale, M. Pal, Bioorg. Med. Chem., 2009, 17, 1783-1802. DOI: https://doi.org/10.1016/j.bmc.2009.01.061
W.J. Metzler, J. Yanchunas, C. Weigelt, K. Kish, H.E. Klei, D. Xie, Y. Zhang, M. Corbett, J.K. Tamura, B. He, L.G. Hamann, M.S. Kirby, J. Marcinkeviciene, Protein Sci., 2008, 17, 240-250. DOI: https://doi.org/10.1110/ps.073253208
G.E. Piérard, C. Piérard-Franchimont, P. Paquet, P. Quatresooz, Expert Opin. Drug Metab. Toxicol. 2009, 5, 1565-1575. DOI: https://doi.org/10.1517/17425250903386269
E. Antoniadou-Vyza, N. Avramidis, A. Kourounakis, L. Hadjipetrou, Arch. Pharm. 1999, 331, 72-78. DOI: https://doi.org/10.1002/(SICI)1521-4184(199802)331:2<72::AID-ARDP72>3.0.CO;2-E
A. Orzeszko, R. Gralewska, B.J. Starościak, Z. Kazimierczuk, Acta Biochim. Pol., 2000, 47 (1), 87-94. DOI: https://doi.org/10.18388/abp.2000_4065
A. Orzeszko, B. Kamińska, G. Orzeszko, B.J. Starościak, Il Farmaco, 2000, 55, 619-623. DOI: https://doi.org/10.1016/S0014-827X(00)00075-6
E. Antoniadou-Vyza, P. Tsitsa, E. Hytiroglou, A. Tsantili-Kakoulidou, Eur. J. Med. Chem., 1996, 31, 105-110. DOI: https://doi.org/10.1016/0223-5234(96)80443-0
A.J. Lin, M. Lee, D.L. Klayman, J. Med. Chem., 1989, 32 (6), 1249-1252. DOI: https://doi.org/10.1021/jm00126a017
C. Singh, S. Chaudhary, S.K. Puri, J. Med. Chem., 2006, 49, 7227-7233. DOI: https://doi.org/10.1021/jm060826x
C. Singh, S. Chaudhary, S.K. Puri, Bioorg. Med. Chem. Lett., 2008, 18, 1436-1441. DOI: https://doi.org/10.1016/j.bmcl.2007.12.074
Y. Dong, S. Wittlin, K. Sriraghavan, J. Chollet, S.A. Charman, W.N. Charman, C. Scheurer, H. Urwyler, J. Santo Tomas, C. Snyder, D.J. Creek, J. Morizzi, M. Koltun, H. Matile, X. Wang, M. Padmanilayam, Y. Tang, A. Dorn, R. Brun, J.L. Vennerstrom, J. Med. Chem., 2010, 53, 481-491. DOI: https://doi.org/10.1021/jm901473s
C. Singh, R. Kanchan, U. Sharma, S.K. Puri, J. Med. Chem. 2007, 50, 521-527. DOI: https://doi.org/10.1021/jm0610043
P. Lorenzo, R. Alvarez, M.A. Ortiz, S. Alvarez, F.J. Piedrafita, A.R. de Lera, J. Med. Chem., 2008, 51 (17), 5431-5440. DOI: https://doi.org/10.1021/jm800285f
Downloads
Published
Issue
Section
License
This work is licensed under a Creative Commons Attribution 4.0 International License.
For all articles published in Prospects in Pharmaceutical Sciences copyright is retained by the authors. The journal publishes articles in the Open Access policy, within the CC BY 4.0 licence.
This is a human-readable summary of (and not a substitute for) the license. Disclaimer.
You are free to:
Share — copy and redistribute the material in any medium or format
Adapt — remix, transform, and build upon the material for any purpose, even commercially.
The licensor cannot revoke these freedoms as long as you follow the license terms.
Under the following terms:
Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.
No additional restrictions — You may not apply legal terms or technological measures that legally restrict others from doing anything the license permits.
Notices:
You do not have to comply with the license for elements of the material in the public domain or where your use is permitted by an applicable exception or limitation.
No warranties are given. The license may not give you all of the permissions necessary for your intended use. For example, other rights such as publicity, privacy, or moral rights may limit how you use the material.
How to Cite
